


My Baby's First Time

by msemmyjones



Series: My Baby [3]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Ass to Mouth, Barebacking, Blow Jobs, Deputy Derek Hale, Dirty Talk, Dom/sub Undertones, Dubious Consent, Humiliation, M/M, Praise Kink, Rimming, Spanking, Underage Sex, and also he cries once or twice, because like always Stiles is a minor
Language: English
Status: Completed
Published: 2014-08-29
Updated: 2014-08-29
Packaged: 2018-02-14 23:25:54
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 8,084
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2207016
Author URL: https://archiveofourown.org/users/msemmyjones/pseuds/msemmyjones
Summary: <blockquote class="userstuff">
              <p>Stiles Stilinski turned twelve on a Wednesday.</p><p>On Thursday Derek Hale made him a man.</p>
            </blockquote>





	My Baby's First Time

**Author's Note:**

> All the usual warnings. Please check the tags, and as always this is unbeta-ed, so sorry for any and all mistakes.
> 
> Also, I take back what I said about Stiles' age being vague. Seeing as this installment includes his twelfth birthday, I guess it's not so vague anymore.
> 
> And lastly, I suddenly feel I need to make the disclaimer that obviously this is not behavior I would condone in real life. Derek should super be going to jail in real life.....

"But Da-ad!"

"Stiles, we talked about this. You're old enough to stay home by yourself. I trust you. And I can't let everyone else work the night shift for me forever. Everyone's gotta do their part including you and me."

"I know, it's just...it's my birthday this week and I..."

"Hey!" Sheriff Stilinski interrupted his son before he could really wind himself up. "Stiles, I took the whole day off for your birthday. We're going to have a whole day of just you and me. And I'm not even going in the next morning."

"Yeah, just the next night," Stiles muttered darkly. He crossed his arms over his chest and pouted, turning his face away. Stiles knew he was being childish and unfair. His father was doing the best he could, and Stiles really was appreciative of the time they would spend together on his birthday. It was just...Stiles didn't like spending time at the house alone, especially at night. It was too empty and quiet now that his mother was dead, and Stiles didn't like spending time with her ghost.

Sheriff Stilinski sighed heavily and rubbed his tired face with his hands. Before he could reply to his son, a beep from outside the office grabbed his attention. "Go pick up that fax for me, Son?" he asked instead.

As he picked up the file in front of him and took another slurp of his coffee - gone cold during his argument with Stiles - a knock came from his door. "Open!" he said, and looked up to see Deputy Hale slide through.

Deputy Hale was one of Sheriff Stilinski's favorites, though if you asked him about it his only response would be _"this is a police station, not a damned popularity contest."_ Hale was a bit of a loner. No family - they had all died in a fire when the Deputy was a teenager. He was diligent and hardworking, patient and kind, but he was quiet and gruff with most people which could detract from his more positive attributes. Stilinski liked to tease Hale about a few of the ladies' (and more than one gentleman's) opinions that his face made up for his prickly personality and see his ears turn red as he glowered back at him. But what really endeared Deputy Hale to the Sheriff was his friendship with Stiles. Stiles was one to chatter on incessantly, and where most people would cut him off Derek listened. Really listened. And, the Sheriff noted, he even became a bit more chatty and relaxed himself when Stiles was around.  Sheriff Stilinski knew they spent time together outside of simply taking care of Hale's dog. Stiles had regaled him with stories of movies and hikes and time spent at the park. He knew both were a little lonely and was glad they had begun to curb that loneliness with each other. It might have been unorthodox, his not-quite twelve-year-old son's friendship with his twenty-six-year-old Deputy, but damned if Stilinski would discourage it.

"What can I do for you, Deputy?"

"This may be a bit presumptuous, Sheriff, but I couldn't help but overhear your talk with Stiles just now."

Stilinski sighed. "When your son's mouth is as loud as mine, you get used to everyone hearing everything. The guys in the holding cell overheard our talk just now. What about it?"

"Well, I just thought I'd offer...I mean, since he's over all the time anyway to hang out with Peter...if staying home alone makes Stiles that uncomfortable, he can always stay with me. I'm working early mornings all this week so I'd have to slip out before 5, but he'd be able to wake up to Peter."

"That's awfully generous of you, Hale."

"Seriously, it's no problem. I've got a guest room. If you're comfortable with it, it's all his."

"Well thank you. I mean it, I really appreciate this. He's old enough now, it's just ever since his mother...well. I'll talk to him and let you know." Deputy Hale nodded at the dismissal and saw himself out.

A few minutes later Stiles returned, fax in hand. "Oh my God, Dad, that seriously took forever. Are they sending you the next Great American Novel?"

 

Deputy Hale had only been back at his desk for about five minutes when he felt a pair of thin gangly arms throw themselves around his neck. "Thank you!" a voice behind him cried. With a smile, Hale turned in his chair and returned Stiles' hug.

"I got big plans for you, Birthday Boy."

 

Stiles Stilinski turned twelve on a Wednesday.

The Sheriff let his son sleep late, then took him out for a breakfast of bacon and waffles. They went shopping for new books and video games, and Stiles screamed when he was presented with his very own laptop. The two went hiking in Beacon Hills Preserve, tossed a baseball around at the park, and ended the day with grilled steak, birthday cake, and Star Wars.

Stiles Stilinski turned twelve on a Wednesday.

On Thursday, Derek Hale made him a man.

 

Stiles stopped dead in the middle of his story about his awesome twelfth birthday. His father was already at work for the night. Stiles and Derek were just finishing up their dessert (Stiles had brought over leftover birthday cake), and Peter was already snoozing on his bed.

"I'm sorry, did you just say you've never seen Star Wars?" Stiles looked at Derek incredulously. How was that possible? Stiles had been convinced that Deputy Hale was the perfect man, and now that image was crumbling before his very eyes. "Who hasn't seen Star Wars?"

"Sorry," Derek shrugged. "Just never got that into it." He took their empty plates over to the dishwasher.

"Oh my God, oh my **God** , we have to fix this. We're watching Star Wars right now."

"We could. This is your birthday, so we'll do whatever you want." Derek stood behind Stiles' chair, threading his fingers through the hair at the nape of the boy's neck. "But I had something else in mind."

Stiles shuddered at Derek's voice, deep and smooth in his ear, and his cock instantly perked up in his shorts. It had been over a month since Stiles had given and received his first blow job, over a month since he begged Deputy Hale to fuck him. So far, despite all their talk, they had stuck to just hand and blow jobs. Stiles was pretty sure that was about to change.

"Okay," he whispered. Stiles cleared his throat in an attempt to make his words sound more confident. "What did you have in mind?"

"I thought you'd like to see my bedroom."

Stiles had been helping Derek take care of his dog Peter for over two months now, spending a portion of almost every day at Derek's house. It had been almost that same length of time that Stiles had been getting naked with Derek. And yet, in all the time, Stiles had never seen the inside of Derek's bedroom. Heart pounding, Stiles got up from the table and followed Derek from the kitchen.

Derek's bedroom was clean and comfortable. The walls were painted a soft sage green, and decorated with art, mostly made from dark woods. He had two full bookshelves, overflowing with books that looked well loved. The top of the dresser was strewn with personal ephemera: receipts and change, his keyring, an expired credit card. In the middle of the mess stood a single framed photo, a teenaged Derek sticking his tongue out at the camera, surrounded by the smiling faces of his family. Against the far wall was Derek's bed, made of dark wood with a comforter and sheets of deep plum. It was an adult's bedroom, and Stiles halted in the doorway in awe that he was being invited in.

Guiding the boy with hands on his shoulders, Derek slowly walked them into the room. He could tell Stiles was skittish, a little nervous about what was to come. "Calm down, Baby," he murmured, running his hands soothingly up and down Stiles' arms. "Take a deep breath for me. Now, have we done anything so far that you haven't liked?" Stiles shook his head. "Okay, then there's no need to worry about this either. Why don't you take off your clothes for me?"

Derek watched the boy strip slowly, his clothes falling haphazard on the floor. He saw that Stiles was trembling now. "Shh, Baby, shhh," he cooed. "You're okay." Standing behind him, Derek let his hands gently roam the boy's body: stroking his soft belly or plucking a nipple. Derek bent down to nose at the boy's throat, inhaling deeply to capture the sweet smell of his baby. "I'm going to make you feel so good. My fingers, my tongue - they're going to touch every inch of you. You're going to feel nothing, **nothing** , but the most exquisite pleasure. I'm going to take you apart piece by piece, and then I'm going to open you up on my cock." Stiles moaned at the filth spewing from Derek's lips, his little cock now fully chubbed up. Derek loved the picture they made, himself still fully clothed in shorts and a t-shirt and Stiles bare naked and hard. "Are you ready, Baby? Ready for your ass to be plugged full of my cock? Is your little hole thirsty for my cum?"

Stiles could barely breathe, he was so turned on. He couldn't even speak, could only whine and nod as Derek thumbed both nipples.

"Good boy. Okay, now I want you up on the bed on all fours." Stiles scrambled to obey, presenting his ass. Derek groaned at the sight of Stiles' creamy pale skin, stark against the dark bedding. Stroking over his own clothed cock he continued, "That's right, spread your legs. As wide as they go." Sliding down onto his elbows, Stiles spread his knees. He was wide open now, face down and hips just hovering over the blanket.

"Good. Now I want you to hump the bed." Stiles blushed and let out a whimper of embarrassment, though he eventually did as he was told. "C'mon, you can do better than that. I know how slutty you really are. Show me you mean it." Stiles whined and humped down harder. The downy comforter felt so good against his aching cock, so silky and soft. Stiles was mortified to know Derek was watching him, but he just couldn't stop. He pressed his body down fully on the bed, fingers twisting in the blankets by his shoulders, and grunted in time with each thrust of his hips.

Walking around to the other side of the bed, Derek pulled on Stiles' hair to lift his face for a kiss. Stiles' hips slowed down as he attacked Derek's mouth, moaning as his tongue was sucked in. The kiss was messy, tongues and lips everywhere. Without warning, Derek reached over Stiles' body and spanked the boy, hard. Stiles let out a squeal of surprise, arms and legs flailing. Pleased with the response, Derek did it again, raining down spank after spank on those juicy cheeks as the boy screamed through his nose. He was overwhelmed with the dual sensations of pleasure and pain, and both pushed back into Derek's hands and tried to squirm away.

When Derek was finished, Stiles' ass was a sweet rosy color. Derek climbed onto the bed, kneeling next to the boy. He palmed those warm, pink cheeks, soothing them with gentle hands. Stiles sighed at the soft treatment, at Derek's murmured words of comfort, and his hips continued thrusting, slow and syrupy.

As his boy relaxed, Derek ever so gently spread his cheeks apart. "There it is. Your little virgin hole. It's so pretty, Baby, so pink and sweet." Stiles squirmed slightly at the praise, embarrassed at just how exposed he felt. He sighed as he felt Derek trace the rim with the tip of one finger. The touch was soft and light as he rubbed over the hole. "It's going to look even better when it's stretched out on my cock." Drawing the finger back, Derek tapped lightly directly on the hole, three times in quick succession. He delighted at Stiles' little jump and keen, and watched as the rose winked just slightly open at each tap. So beautiful, Baby. I just have to taste it."

Before he even had time to process the meaning of those words, Stiles felt something wet, warm, and pulsing press against his hole. Stiles moaned long and loud as he realized it was Derek's tongue. Derek was still holding open Stiles' rosy cheeks, and using his tongue to lick long, fat stripes down the crack and over Stiles' hole. It felt good, it felt **so** good.

Pulling back, Derek ran two fingers more incessantly over the hole. He grinned as he drank in Stiles' throaty whines and groans, watched him pushing his ass back into Derek's hands searching for more. "You like my tongue, huh Baby?" Stiles squealed in response as Derek surprised him with another quick spanking before gently dragging his tongue back over Stiles' hole.

"Do me a favor, Baby, okay?" Derek's lips tickled against Stiles' hole. "I want you to relax your hole, can you do that?" Counter-productively, Stiles' whole ass instinctively clenched at the words. "You can do it, Baby, just relax and let me see your little hole open for me." Stiles took a big breath in and Derek could see his ass muscles clenching. But then Stiles slowly, slowly, let the breath out, and with a ripple along his body completely relaxed, his little hold gently unfurling.

With a laugh, Derek dove down to kiss the hole, and when he pulled back saw the little starburst tightly furled again. Taking two fingers, Derek brushed lightly up and down the area below the hole, gently tickling Stiles' taint. With a whine, Stiles canted his hips up, searching for more of Derek's tongue. Instead Derek reached between Stiles' legs to pull his cock through, stroking it a few times before bending down to suckle the head.

"Please," Stiles moaned, unsure exactly what he was begging for, just knowing he needed more. Derek's only response was to tongue the slit - savoring the bitter taste of Stiles' precum - and reach out to squeeze Stiles' little full sac. He rolled the balls in his palm, jiggling and squeezing them, listening to Stiles' increasingly desperate moans.

"You're doing so well for me," Derek crooned. Reaching up, Derek tugged his t-shirt over his head, leaving his shorts on for the time being. Two fingers trailed down Stiles' crack to again come to his hole. As he rubbed against the hole steadily - up and over, around the rim, a gentle press in - Derek leaned over to pepper Stiles' face and shoulders with kisses. He mouthed wetly at the boy's throat as Stiles let out thick, shuddery pants.

"Did you know your ass would taste so good?" Derek asked, lips brushing over the ridges of Stiles' ear. "I did. I was sure of it. A pretty boy like you had to have the sweetest ass." Stiles bit his lip to stifle a groan. "No don't, Baby. I love your noises, love hearing how good I make you feel. Do you like my tongue on your little hole?"

Moaning, Stiles nodded.

"You're in luck, Baby, because I'm not done with your whorehole yet." At this, Derek swung a leg over the boy, basically straddling Stiles' shoulders. Leaning forward, Derek again pried open the boy's cheeks, rolling them in his hands. Pulling his hands back, Derek let loose a series of sharp, quick spanks, marveling at the juicy cheeks' jiggling and Stiles' pained "uh...uh...uh..." timed with each hit.

"Get your hips up, Baby." Stiles struggled to hold his hips up higher, weighted down with Derek's body on top of him. Pulling the lifted cheeks apart one more time, Derek dove in, this time with no reservations. Stiles shrieked as Derek's tongue didn't just lick over his hole but pushed its way in. Using his lips as much as his tongue, Derek kissed and sucked Stiles' hole. His tongue fucked in deeper and deeper, wet and wriggling, his stubble prickling the sensitive skin.

Pulling back to catch his breath, Derek ran his hands down the boy's calves to his ankles. His thumbs made soothing circles on the balls of Stiles' feet as he pulled them together in a frog-like pose. Raising up slightly and leaning even more forward, Derek brought one foot to his mouth. He kissed over the arch and sucked a few toes into his mouth, wetting the webbing with his tongue. "God, Baby, even your little feet are beautiful."

Stiles whimpered piteously. His head was spinning with arousal. He needed to cum so badly. And Derek's mouth felt so good on him. Everywhere. Stiles was pretty sure he might be able to cum just from Derek sucking on his toes. He didn't think something like that would have felt so good, but it did. Just soft, gentle sucking and a warm tongue squirming between his toes. It was a nice respite from the intense pleasure of Derek's tongue in his ass.

That respite didn't last long, however, as Derek was soon once again buried in Stiles' ass. This time he held nothing back, nipping around the rim, pushing his tongue in deep before pulling out for quick dips in. He growled deep in his chest, wrapping his arms around Stiles' waist to haul the boy's hips up higher. Saliva leaked out of Stiles' hole, dripping down his taint and balls. Derek pushed his tongue deep into the hole, as deep as he could go, pulsating in the heat and wiggling like it was alive. Stiles gripped onto Derek's ankles where they were bracketing his head. Stiles thought he was going to come apart. This was too much, the pleasure was too intense. He didn't think he could take anymore. With one last spank, Stiles howled beneath Derek as he came on the blankets below.

Slowly, gently, almost reverently, Derek leaned back and pulled Stiles up and out from under him. He cradled the boy to his chest, running soothing hands up Stiles' arms. Stiles was trembling, overwhelmed by the immense pleasure he had just experienced. Derek ducked his head and softly kissed his lips. He peppered the boy's face with kisses - his cheeks, his nose, and eyelids covered with soft kisses - all while murmuring in his ear. "You were beautiful, Baby. So good. I'm so proud of you. I was going to reach around and jerk your little cock off but I didn't have to. You came right on my tongue."

When he was finally able to speak, Stiles looked up and said, "You didn't fuck me."

Derek laughed. "Not yet, Baby. But there's still time. I needed you loose before I plugged you up with my cock. Needed you to cum first."

"Oh." Stiles let his body melt against Derek's as the man sucked gently on his neck. "Mmmm..." he sighed, happily relaxed. "So you're still gonna fuck me?"

"Only if you want, Sweetheart. It's your birthday, right? I meant for us to, but I didn't mean to get so carried away making you cum first. Your ass was just too sweet. I couldn't help myself!"

"Okay." Stiles closed his eyes and rubbed his face against Derek's hard chest. "Give me a minute? I think I still want you to fuck me."

"Anything for you, Baby." Derek tilted Stiles' face up and kissed him again, deep and slow. These kisses were sleepy and sloppy, wet lips lazing against each other. Derek offered Stiles his tongue, and he took it fully, letting it fill his mouth and his senses. He sucked on it hungrily.

Still kneeling, Derek lowered his body down to be resting fully on the backs of his legs. Without ever letting their lips part, he pulled Stiles so the boy was fully in his lap. Derek groaned as Stiles shifted, his ass rubbing against Derek's still clothes cock, hard and wet in his shorts. Grabbing onto Stiles' ass for balance, he bucked his hips up, grinding their bodies together. Stiles wrapped his arms around Derek's neck and let his body be used, losing himself in Derek's kisses.

Slowly - so slowly Stiles didn't realize it was happening - one long finger snaked down between his cheeks and came to rest right on the rim of his hole. With movements so miniscule and gentle, the finger circled the hole. Stiles sighed into Derek's mouth, relaxing subconsciously at the finger's ministrations. Then slowly, still so slowly, Derek's finger began to push in.

With a noise of surprise, Stiles broke the kiss and pulled back to stare at Derek, wide-eyed. Derek himself said nothing, just held Stiles' gaze until his middle finger was fully buried inside his boy. Then, just as slowly, he pulled his finger back out again. In. And out. In. And out.

"You're inside me," Stiles finally whispered.

"I am." Derek leaned forward for another kiss. "Your little hole opened right up for me. It's a slutty hole, just like I thought." Derek had actually expected there to be more resistance at this first breach. But Stiles' ass was still so wet from their previous activities, not to mention loose and relaxed from his earlier orgasm and their current makeout session, that Derek's finger was able to slide in easily.

Derek continued the slow glide of his finger, but at the moment didn't add anymore. While Stiles admitted to himself that the feeling of the finger inside him was a little weird, he also realized how much he liked the rhythmic pushing and pulling on his sensitive rim. And he appreciated knowing it was Derek inside of him, Derek touching his insides. Stiles glowed with that knowledge, and canted his hips back slightly wanting to be filled with more of Derek. He whined when instead the finger was removed.

Derek was pretty sure he was going to cry if he didn't get some relief for his dick soon, so none too gently he wrestled Stiles back onto the bed. Flat on his back, arms above his head and held together by the wrists in Derek's hand as he hovered over him, legs spread - Stiles made a mouth-watering picture of corrupted innocence. Derek lowered himself down onto the boy whose legs instinctively wrapped around his waist, little cock - hard again from the fingering - grinding against his own. But it wasn't enough. Derek reared back and quickly, **finally** , shucked his own pants.

Now fully naked, Derek attacked his boy like an animal. Stiles moaned as Derek grinded their hips together, his body fully covering the boy's. He sucked bruises onto his smooth, pale chest and shoulders and bit down on little, sensitive nipples.

"God, you're so fucking sexy, Baby. I can't wait to bury my cock in you. You're going to feel so good on my dick, so wet and tight." Stiles writhed under Derek's assault, unable to do anything but surrender himself to the pleasure of Derek's body on his.

Pulling himself off, Derek grabbed Stiles' ass and hauled his hips up, bending the boy nearly in half - ass in the air, knees back by his ears. "Derek...oh my God, oh my God, Derek!" Stiles wailed as Derek sunk his tongue back into his still sloppy, wet hole.

With one last hard kiss to that juicy hole, Derek pulled off and sat back on his haunches, letting Stiles' body drop unceremoniously down to the bed. "Come here, Sweetheart. Crawl over here and get my dick wet."

Clumsily, Stiles clamored up onto his hands and knees and crawled over to Derek. From his position he looked up, mewling meekly, and head butted Derek's hip, nosing into his groin. Derek grinned at the boy's kitten-like affection. Lowering himself to his elbows, Stiles got to work sloppily mouthing at Derek's cock, licking and kissing at the shaft and balls below. Eyes closed and head back with pleasure, Derek breathed deeply. "Good, Baby. So good to do what you're told." Stiles' whole body wriggled at the praise, so pleased to make Derek so happy.

Without Stiles noticing, Derek reached back under the pillows and retrieved the lube he'd stored there earlier, coating his fingers. Stiles' face was buried in Derek's crotch, making happy slurping noises, and his ass waved high in the air. With Stiles happily distracted with his cock, Derek brought one slick finger back to the boy's hole. Stiles froze, then let out a long, low moan as the finger pushed in, only stopping when it was fully hilted.

"You like that, Dirty Boy?" Derek asked, grinning wickedly as he began to pump his finger in and out.

"Yes, yes, yes," Stiles panted into Derek's stomach, one hand reaching up to take over for his mouth. He jerked Derek off in time to his finger, moaning constantly.

Without warning, Derek fed a second finger into Stiles' hole, the clench tighter but the glide still smooth and easy. "Oh God, oh God, yes!" Stiles canted his hips up, trying desperately to get those fingers deeper. While the first finger may have felt weird, two was like Heaven. Derek was stroking his insides and they were on fire for more. Stiles knew he needed to be filled, knew two fingers was not going to be enough. He needed them deeper, he needed them thicker, he needed Derek's cock.

Though it wasn't where he needed it, Stiles took hold of the thick shaft and sunk his mouth down, moaning anf drooling down Derek's cock.

"Need it bad, don't you, Baby? Your slutty ass is just begging for my cock, begging me to split you open and fill you up."

Derek tangled the fingers of his free hand in Stiles' hair and held him steady, allowing the boy to calm down; two fingertips just breaching his hole and only the cockhead for him to suckle. Once the boy was still, Derek slowly fed him his cock, the head just entering his throat. They'd spent the summer working on Stiles' deep-throating techniques, and while he still couldn't take it all, he was making big improvements. He could feel the boy swallowing around him. Keeping his eyes locked on Stiles' eyes, glassy with desperation and lust, Derek slowly pushed in a third finger.

Stiles screamed around the cock in his mouth. He could feel his hole stretching to accommodate the three big fingers forcing their way inside. It was harder this time, so much harder to get all three to fit, and it burned. But Stiles felt so good. He was full on both ends, stuffed with Derek's cock and his fingers, and he didn't think anything could ever feel better than this. And then Derek twisted his fingers just so and Stiles knew he's been wrong.

White hot pleasure coursed through Stiles' body and he jolted like a live-wire. Derek's cock pulled free of his mouth with a wet squelch and Stiles wailed at the loss while simultaneously humping back onto Derek's fingers.

"Pleeeeease!" he begged. "Again, again, again, please. I'll be good, I'll be so good. Please let me be your good boy, just touchmetouchme **touchme**!"

Instead, Derek pulled his fingers out. Stiles moaned unhappily, hips searching for anything to fill him. "Please," he sobbed.

"Shhh..." Derek cooed, pulling his boy up to wrap his arms around Derek's neck. Stiles sagged against him, trembling with need. Derek's big hand soothed over his boy's body, thumbs gently rubbing his nipples. "Don't worry, Baby. I still have to fuck you." Stiles shivered with anticipation.

Holding the boy close, Derek kissed him sweetly. "But first," he said, "I need you to do something for me. I need you to look at me and tell me how you feel."

Stiles stared as his mind raced to answer the question. How did he feel? He felt good, he felt horny. He felt empty, missing Derek's fingers and cock. He felt guilty because this relationship had gone was passed the initial plan and he was sure his father would disapprove. He felt special and cared for and safe. He felt overwhelmed with both pleasure and his emotions. He felt scared. He felt dirty. He felt cherished. He felt...

"I love you."

Derek's eyes widened in surprise. He had only asked to check in with Stiles, make sure he was doing okay. And he liked listening to the boy talking through his discovery of his sexuality. He was not expecting a declaration of love. He looked back at Stiles, eyes wide and trusting. A crackle of electricity rushed through Derek's body and he felt warm and light. He smiled.

"I love you too, Baby."

Gently, Derek lowered Stiles to the bed. He positioned himself between the boy's legs and sank his mouth down on his cock, sucking gently. Stiles arched his body with a sigh of relief as he was once again filled with three big fingers.

When his fingers could glide easily, scissored apart or not, Derek pulled out again. Pushing back on Stiles' knees, he raised that juicy ass in the air. Without being prompted, Stiles grabbed his own legs and held them there, spread wide. Reverently, Derek licked over the hole.

"Please," Stiles whined. "Please."

Derek lowered him down again and crawled over him, covering Stiles with his body. He kissed him deeply and gently dragged their cocks together. Resting his forehead against his boy's he asked, "Are you ready for me?"

Stiles nodded.

Pulling himself back up to his knees, Derek quickly slicked his cock. He took a firm hold of it in one hand and raised Stiles' leg up to his shoulder with the other, Stiles' other leg wrapped loosely around Derek's waist. He let his lubed cock kiss the hole a few times teasingly, just a gentle press and release. Finally, in response to Stiles' impatient whine, he pushed in.

Stiles' body spasmed at the breach. His arms jolted and flailed at his sides as if unsure what to do, fingers clenching and unclenching in the blankets. His eyes were wide and looked shocked by what was happening to him, tears welling up at the stretch. His mouth had fallen open in a silent cry, to overwhelmed to make any actual noise.

If Derek Hale was a better man, the sight of those tears would have stayed his hand. He would have stopped, would have pulled out. But Derek Hale was not a better man and Stiles Stilinski was beautiful with tears on his face. Slowly and steadily, the glide smooth and tight, Derek pushed until he was buried in Stiles' heat, hips flush with Stiles' ass.

"I'm in, Baby. How does it feel?"

"Big," Stiles moaned. "It's so big." He was right. Derek's fingers were nothing compared to his fat cock. Fully sheathed, Derek stayed still, giving the boy time to adjust to the intrusion. Stiles gritted his teeth and breathed deeply as he continued to moan, "So big, it's so big, so big in me."

Stiles' whole body was buzzing. It was as if every nerve had rewired itself to be directly linked to his ass - specifically his hole which was now stretched wide. It hurt. It burned. His tears were a testament to just how much he was stretched. But at the same time, it felt so good. He was filled, stuffed full, with Derek inside him. As the two lay still, Derek looked at Stiles with such tender affection that it actually helped ease the hurt to a dull ache. Soon, Stiles relaxed and was able to breathe a sigh of relief.

During this time, Stiles own little cock never flagged. Derek reached out to give it a squeeze, a reward for taking Derek so well. Stiles let out a wet moan at the contact, and Derek took that as his cue to start moving. Slowly, he pulled out and pushed back in. Over and over he pulled out and pushed back in - long, steady strokes. Stiles himself could do nothing but moan continuously, his entire being reduced to nothing more than his hole, clinging to Derek's cock.

Derek, for his part, was much more vocal. Using his free hand to grab Stiles' leg from around his hip, he spread the boy wide and let loose a litany of filth.

"God, Baby, look at your little hole taking my cock. You're split so wide. Your little ass is just gobbling me up. I knew you'd be a hungry boy. Knew your ass would be just as slutty as the rest of you. And God, you're so tight. So tight. Little hole just squeezing around me, trying to milk my cum out, aren't you?"

Finally able to speak again, Stiles moaned out the words Derek was hoping to hear. "Oh God...so good!"

That admission of pleasure was all Derek needed. Lowering himself down to cover his boy and kiss him soundly, Derek snapped his hips and began pounding into Stiles at a punishing pace. Stiles wrapped his arms and legs around Derek and buried his face in his shoulder, wailing, overwhelmed at the feeling of fullness.

Derek was in Heaven. He'd never been in an ass this tight. He could feel it stretching to accommodate his impressive size - could feel the glide getting smoother as the boy relaxed and welcomed him in. Stiles was hot and silky and he could feel the rim cling to his cock every time he pulled out, like it couldn't stand not being filled.

"I'm so proud of you," Derek panted. "Doing so good, Baby. You feel so good around my cock." With wild abandon, he devoured Stiles' body: petting his face and throat, peppering his chest with kisses, teasing a pebbled nipple in his teeth. He traced the boy's moles with his tongue, relishing the taste of salty sweat-slicked skin. Stiles arched into his touch, his body responding of its own accord to Derek's worshiping.

With a deep kiss, Derek slowed his frantic thrusting. Burying his himself deep in Stiles' ass, he grinded his hips as Stiles relaxed around him. Derek's tongue filled the small mouth below him as he re-angled his cock, searching for Stiles' prostate. He grinned when Stiles' howl of pleasure let him know he'd found the right spot. Kneeling up to grab hold of the boy's hips, Derek rabbited into that one spot, hitting it over and over again.

"Yesssss...yesyesyes. Oh my God, yes. So good. So good, so good, yes!"

 Abruptly, Derek pulled out. Stiles keened high and loud, body writhing into the covers at the unwelcome feeling off emptiness. Laying himself down on his back, Derek pulled Stiles up and over him. The boy squatted down and fed Derek's cock back into his hole, but it wasn't enough. The angle was all wrong, he couldn't go very deep, and Stiles was uncoordinated at the best of times. Stiles whined high in his throat, hips working desperately to get Derek's cock buried back inside of him.

"Please," he begged. "I need it! Please, Derek, please!"

"What do you need, Baby?" Derek teased.

"Need your cock. Need it in me, I'm so empty now!"

Derek could not believe some of the words that would come out of his dirty baby's mouth. His little virgin was a natural. He pulled the boy down to lay on top of him, knees on either side of his hips, and fucked up into him, deep and slow. Stiles moaned his relief at being filled once more.

"There you go, Baby. There's my fat cock filling your little hole."

"Thank you," Stiles whispered. He panted into Derek's neck as he let the pleasure of Derek's cock filling his ass wash over him.

Eventually, Derek's hips slowed, and Stiles whined unhappily when they stopped altogether.

"C'mon, Baby," Derek cooed. I can't do all the work, can I? You wanna be fucked, I wanna see you earn it. Fuck yourself back on my cock, Baby, let's see your slutty ass work for it."

Stiles hauled himself up only shaky arms and tentatively pushed his hips back.

"Mmm..." Derek groaned. "I know a cock-hungry whore can do better than that. You're not getting anything else until you prove you're a good cockslut."

Whining high in his throat, Stiles picked up speed until he was slamming himself back on Derek's cock. His head hung down between his shoulders, sweat glistening on his brow. Stiles was desperate for Derek's cock to fill him, to keep filling him, to touch all those mystery places inside him. He rolled his hips, little hole sucking Derek in deeper, and Derek marveled at how beautiful he looked.

The current angle was just now enough. He needed more. Pulling himself fully up onto his knees, Stiles sank all the way down, impaling him fully on Derek's cock with a cry of relief. His thighs trembled as he clumsily worked himself into a rhythm.

Derek threw his head back and groaned. "Yes, Dirty Boy, ride me. I wanna see you bounce up and down on my cock. Are you all filled up now?"

"Yesyesyesyes," Stiles cried. "So full. Please, please I'm a good boy. I'm a good boy, I need it. Please fuck me!"

Derek looked up at Stiles who was absolutely writhing on his dick, hole clenching down with every drag up. He was beautiful: face red and flushed, mouth open, little cock bobbing wildly between his legs. Derek grabbed hold of Stiles' wet cock and thumbed the head.

The dual pleasures were too much for Stiles. Overwhelmed, the boy wailed and burst into tears. He fucked himself down faster on Derek's dick, sobbing, "Please please please, I'm a good boy, I'm a good boy!"

With hands rubbing soothing circles into his back, Derek pulled Stiles down to his chest. He wrapped his arms protectively around him, letting the boy snuffle into his shoulder, and shushed him. Long, deep thrusts of Derek's hips soothed Stiles, keeping him filled but calming the intensity of his pleasure.

"You're okay, Love." Derek listened as Stiles' shaky breath evened out, interrupted by the occasional wet hiccup. "You're okay. And you are a good boy. You're **my** good boy. I'm so proud of you, Baby. You're doing so good for me. You just got a little overwhelmed."

"Too much," Stiles agreed. Clinging to Derek, he nuzzled further into the man's shoulder, relaxing into the steady rhythm of his hips. "Liked it though," Stiles continued. "Liked being all filled up."

"I'm glad, Baby. I like making you feel good." Derek turned his head to gently kiss Stiles' wet face. "And your ass feels so good around me. Like it was made just for my cock."

Stiles shivered, letting out a little moan as Derek's cockhead brushed gently passed his prostate. "Just yours," he breathed.

"All mine," Derek agreed. "My good boy."

By this time, Stiles had calmed down considerably, and while he could happily spend a whole day just being gently filled with Derek's warm cock, his own little cock really wanted to cum. He began to roll his hips back- tentatively at first, but then more confidently - meeting each of Derek's deep thrusts. "Fuck me again, Derek?" he asked meekly. "Please?"

 Derek surged up and attacked Stiles' mouth, kissing him deep and messy. He let his tongue fill the boy's mouth, capturing his taste. Pulling back, he gave a playful spank to Stiles' ass and helped him climb out of his lap.

"Nooo!" Stiles whined as Derek slipped out of him. "Back in, back in!"

"Calm down, Babyslut," Derek laughed. "I'll be back in that greedy ass soon enough. Now get on your knees and present."

Stiles paused, confused. "Do...what?"

"C'mon Little Boy, just like you did when we started, when you moaned so pretty for my tongue. Hands and knees, face down, ass up, presented to your **master**!" Derek smirked teasingly as Stiles blushed at the word.

Grumbling under his breath, "Please, like you could handle all of this. I'm a handful," Stiles maneuvered himself into position, back arched, ass wiggling enticingly. After a few seconds of nothing, Stiles started to squirm under Derek's scrutiny, embarrassed by the shameless position.

Finally Derek reached out and took Stiles' plump cheeks in hand, pulling them apart and massaging them gently. He took in the sight of Stiles' now well-used hole. It was red an puffy around the rim from the abuse it had already taken. Derek groaned thinking of the pounding still to come.

Bending down, Derek licked a soft stripe over the hole, soothing the tender flesh. He grinned at Stiles' pleased whine and pulled back to blow on the wet rim watching it twitch excitedly. "Couldn't help but take a taste, Baby."

Kneeling up close behind Stiles, Derek took a firm hold of cock, newly re-slicked, and smacked the head down against Stiles' hole. Laughing at Stiles' surprised squeal, he did it a few more times. The hole made a wet squelch as it tried to suck the head inside.

"What are you doing, dude, put it in! Teasing isn't nice!"

Stiles' words broke off into a long moan as Derek thrust in, bottoming out without warning. "There you go, Babyslut, that what you wanted?"

"Yesyesyes," Stiles began, but then, "NOOOO!" when Derek pulled out again completely.

"Not enough?" Derek smirked, pumping his cock in and out once more. Stiles' hole clenched around nothing, desperately trying to keep that cock inside.

Derek thrust his cock in and out of Stiles' hungry hole a few more times, alternating with several sharp spanks on the boy's bouncing cheeks, and reveled in the desperate mewls he heard. Unable to take anymore teasing, Stiles hauled himself up onto his hands and glared back at Derek. "God dammit, Asshole, I thought you were going to fuck me. Fuck me!"

A beat of stillness and silence passed between the two until Derek grinned wickedly. He was on Stiles in an instant, pushing him face-down onto the bed, and pounding into the boy who could do nothing but wail, blissed out at the feeling of being fucked hard. Derek was relentless, fucking into Stiles with suck strength his ass was sure to be bruised in the morning from the pounding of Derek's hipbones. Their bodies came together with a loud slap, slap, slap. Derek's full sac swung between his legs, and Stiles could feel it slam against his taint. Stiles moaned, unable to speak from the animalistic fucking he was receiving. The wet fullness of his ass, the slick glide of his channel, and the tight stretch of his hole became his whole world, bathing him in pleasure.

"That's right, Babyslut, take my cock. Just open up for me. You're right where you belong, ass up and getting fucked." Derek grunted as his hips kept up their brutal pace. "Made for this, Dirty Boy. Made for my big cock."

Roughly, Derek hauled Stiles up off his arms and back onto his hands. He grabbed onto Stiles' shoulders for leverage, slamming him back even harder on his dick. The change in angle caused Stiles to howl as his prostate was hit with every thrust.

"Little hole is so greedy for it," Derek continued. "And I'm gonna wreck it. You want that, Baby?"

"YESYESYESYES!"

Clamoring back down to his elbows, Stiles frantically fucked himself back onto Derek's cock. His ass was bouncing and meeting Derek's hips thrust for thrust. Derek could see the boy was getting himself worked up again. Moans were being pushed out through gritted teeth and movements were becoming more and more desperate. Without slowing his hips down, Derek spanked those bouncing cheeks. Hard.

Stiles screamed. Face smooshed into the blankets, flushed red with exertion, Stiles screamed. His hole clamped down on Derek's cock with every hit. It felt like Heaven, that velvet vice-grip.

"Please," Stiles sobbed, face again wet with tears. "Please let me cum. Need to cum, need to cum, pleeeeeeeease."

"Shhh..." Derek said as he pushed Stiles down flat on the bed until on his lush ass was raised. "You're gonna cum, Baby."

Derek's hips began to slow in an attempt to sooth the boy, but Stiles only became more hysterical. "Nononono!" he screamed. "More, need more. Fuck me, make me cum. Pleasepleaseplease!"

"Shhh..." Derek whispered again. He kept his hips moving, steady but slower, as he kissed over Stiles' back and shoulders. Stiles squirmed at first, desperate to cum, but he calmed soon enough under Derek's gentle ministrations.

"Good boy," Stiles moaned. "I'm a good slut. Please please please let me cum."

With one final kiss between the shoulders, Derek hauled Stiles upright on his knees. Stiles sobbed in satisfaction as he sank down on Derek's cock. Derek wrapped one arm around Stiles chest to keep him upright, tweaking a nipple in the process, and the other reached down for the boy;s wet cock. Stiles threw his head back in ecstasy as Derek tugged on it, stroking in time with his thrusts.

"This what you wanted, my love?" Derek asked.

"Yesssss," Stiles hissed. "Oh God, yes. So good."

Derek bent down to lick the boy's ear. "And what do you say when someone gives you their cock for a birthday present?"

"Thankyouthankyouthankyou!" Stiles panted. He could feel the tell-tale fire in his belly. He was so close. "Oh God. Thank you for fucking me. Oh God oh God oh God. I'm gonna cum!"

"That's right, Babyslut, cum with my cock in your ass."

Stiles shuddered as he felt himself shoot and clamp down hard on Derek's cock. This was a new feeling. A good feeling. He definitely liked cumming with his ass filled.

When he felt Stiles sag against him, fully spent, Derek pushed the boy back and with a roar, took his fill. Stiles moaned and shuddered around him, body oversensitive but too sated to care. It only took a few minutes of Derek pounding into Stiles' soft body before he came. Starting out deep inside the boy, flooding his hot channel, Derek pulled out to paint the swollen hole. He groaned, milking the final drops out, as he watched his cum cling to the puffy rim and drip down the empty balls.

Crawling up the bed, Derek raised up Stiles' sleepy face and brought it to his softening cock. "Clean me up, Babyslut."

Meekly and wordless, Stiles opened his mouth and let Derek feed him his wet cock. He closed his eyes as he suckled, centering himself on the bitter taste in his mouth. He whined when Derek gently pulled himself out, wanting more of the safety and love he felt with that weight on his tongue.

Derek kissed the boy softly before climbing off the bed. He padded into the adjoining bathroom and returned with a wet washcloth. Stiles let himself be turned over onto his back and allowed Derek to wipe down his teary face and sweaty body, but he protested when Derek reached for his ass.

"No," Stiles said. "I want to sleep with you in me."

"Stiles, I'm not just in you, I'm on you. I'm all over you." Derek laughed gently. "I made a big mess of you. Let me clean you up, you'll be all sticky in the morning otherwise."

"Then I'll deal with it in the morning," Stiles insisted. "I like it. I like wearing you, feeling you in me. It makes me feel like I'm yours, even if no one else knows it."

Derek abandoned his washcloth and climbed back onto the bed, maneuvering Stiles so they could both be under the covers. Derek reached up to turn the lights off, and in the darkness pulled his boy close to him.

"You are mine, Baby," Derek whispered as Stiles buried himself more fully into his embrace. "I didn't mean for it to happen. Shit, I will get into so much legal trouble if anyone ever find out. But I did. You're mine now. My baby." He paused, kissing Stiles' hair softly. "And I'm yours too you know, Sweetheart. I love you."

"Love you too," Stiles yawned. "Go to sleep now. Tomorrow you have to get up early and go fight bad guys. And then be ready when you come home."

"Be ready? For what? You think your ass can take me again so soon?"

"Nope. We're watching Star Wars."

**Author's Note:**

> So that's that, I guess. Stiles is a man now. Sort of.
> 
> That was a lot longer than I originally planned. And fluffier. I'm not exactly sure where that declaration of love came from. But I'm kind of okay with it. I think. I may have to rethink some of my plans for this series. Initially it was going to be a bit darker, with Derek being a lot more manipulative. But I think I'll keep with the sweetness.
> 
> Also, let me know if there's anything particular you'd like to see. I may be keeping it sweet but that doesn't mean I can't dive deeper into kinkiness. Maybe the two need to branch out to include more people in their shenanigans. Like Derek's new partner Deputy Parish or his newly adopted son Isaac. Maybe Peter needs to get in on the action (which was the first entry of the series that I wrote which will need to be SUPER rewritten before posting). Maybe we need to tie Stiles up. I can't guarantee I'll write all of them (or any of them), but I'm more than open to suggestions.
> 
> Thanks for reading!


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